Potassium Carbonate → HCID 22678821, compound

HRID 1837610Notes

Reaction equation

HRID 1837610 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][N:15]=2)=[O:9])[N:6]=1.[CH2:19]([C:21](I)(CC)[C:22]([O-])=[O:23])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH:16]([C:13]1[S:12][C:11]([NH:10][C:8](=[O:9])[CH2:7][C:5]2[N:6]=[C:2]([N:1]3[CH2:20][CH2:19][CH2:21][C:22]3=[O:23])[S:3][CH:4]=2)=[N:15][CH:14]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11323531HCID 11323531, compoundHCID 86759523HCID 86759523, compound

Product 1

HCID 22678821HCID 22678821, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.8 g (0.01 mol) of 2-(2-amino-1,3-thiazol-4-yl)-N-(5-isopropyl-1,3-thiazol-2-yl)acetamide, 4.84 g (0.02 mol) of ethyl-iodobutyrate and 2.76 g (0.02 mol) of potassium carbonate in 50 ml of absolute ethanol was stirred under reflux for 5 hours. The mixture was cooled and filtered, and the salts were washed with two 20 ml portions of ethanol. The ethanol was removed at reduced pressure and the residue was dissolved in 100 ml of CH2Cl2. The solution was washed with 30 ml of water, dried, and the solvent was evaporated. The residue was purified by chromatography on silica gel, using CH2Cl2:MeOH 95:5 as eluent, to give the title compound in 30% yield (1.05 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe salts were washed with two 20 ml portions of ethanol
  5. customThe ethanol was removed at reduced pressure
  6. dissolutionthe residue was dissolved in 100 ml of CH2Cl2
  7. washThe solution was washed with 30 ml of water
  8. customdried
  9. customthe solvent was evaporated
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9cd56d83b865405b8e6b072dbcb4cce0
Source dataset
uspto-grants-2004_08
Patent number
US06784198B1

Reaction notes

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